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Graphical Abstract: Eur. J. Org. Chem. 10/2009
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200990022
Subject(s) - chemistry , stereocenter , alkene , stereochemistry , tubulin , intermolecular force , fragment (logic) , microtubule , sequence (biology) , yield (engineering) , diene , combinatorial chemistry , molecule , biochemistry , microbiology and biotechnology , organic chemistry , physics , enantioselective synthesis , biology , computer science , programming language , catalysis , thermodynamics , natural rubber
The cover picture shows the intermolecular interactions between the marine‐derived dictyostatin and the β‐tubulin binding site, as well as some important molecular fragments of the required 15‐step sequence to produce the C11–C23 fragment (highlighted in blue) of dictyostatin in good overall yield. Dictyostatin, an unsaturated 22‐membered macrolactone containing 11 stereocenters, a (Z)‐alkene, and two diene systems, exhibits potent antitumoral activity as a consequence of its reversible and specific binding to the β‐tubulin cavity and modulation of microtubule function. Details of the synthesis and characterization of the C11–C23 fragment are reported in the Short Communication by L. C. Dias et al. on p. 1491 ff. The authors thank Ms. Lívia B. Salum for her contribution to the design of the cover picture.